The question isn’t whether Google collaborates with Democrats, but how Google collaborates with Democrats.

We know that Obama campaign manager Jim Messina received personal mentoring on both technology approaches and management style from Google executive chairman Eric Schmidt, his friend since the 2008 campaign. We know that Google employees overwhelmingly contributed to Democrats in the last cycle (and aggregate individual employee contributions outnumbered the company’s PAC contributions). We know that Google vice president and “chief Internet evangelist” Vint Cerf received a presidential appointment to the National Science Board following last year’s election.

Is it paranoid to believe that Google is deeply invested in helping Democrats? No.

Still, I decided to take a deeper look at the connections between Google and the Obama campaign.

Jim Messina called on Google’s Eric Schmidt, Apple’s Steve Jobs, and Hollywood’s Steven Spielberg for their advice on building an organization. Schmidt gave Messina what turned out to be an invaluable piece of advice:

Messina said Google Chairman Eric Schmidt gave him simple advice: “You do not want political people, you want smart people who you are going to draw what you want and they’re going to go build it.” So Messina went out and hired someone to head the data department who had never worked on a campaign before.

What better pool of talent to draw from than Schmidt’s own company? Schmidt himself certainly wasn’t shy about being deeply involved with the campaign. He even helped himself to the first slice of a cake, purchased by Obama campaign Dev Ops Director Scott VanDenPlas, emblazoned with “Don’t F*ck This Up.” Schmidt later told Bloomberg Businessweek that the Obama campaign was the “best-run campaign ever.”

Google’s Schmidt also personally visited OFA’s Chicago HQ, where he spent time with OFA Chief Technology Officer Harper Reed and OFA Engineer Mark Trammell – Schmidt is the guy with the official OFA lanyard with photo in the mom jeans sitting on the table in the photo below, Reed is in the background by the smiley face, and Trammell is on the far right with the Santa Claus Starter Kit™ beard:

Michael Slaby, OFA’s Chief Integration and Innovation Officer, was a panelist (PDF) at left wing (of course) activism conferences at Google headquarters in Mountain View, CA, which should not be surprising since he was also the chief technology strategist for Eric Schmidt’s venture capital fund, TomorrowVentures LLC. Call me crazy, but I’m guessing their paths have crossed a time or two, and that their conversations have probably had quite a bit to do with politics and policy.

Obama’s impressive data team also boasts a large number of high-profile connections to Google, starting at the top with Rayid Ghani, OFA Chief Scientist. Not only has Ghani keynoted an address at Google Research Labs, according to his online CV (PDF), but he also spoke this month at his grad school alma mater Carnegie Mellon University in a lecture series sponsored by – you guessed it – Google. Ghani’s former department at Carnegie Mellon boasts seven alumni on Google’s payroll on their website.

Ghani’s role on the Obama campaign was to direct Project Dreamcatcher, which used “text analytics to gauge voter sentiment” about issues and speeches. I wonder how he came up with that idea? Could it have been in talking with Katharina Probst, Senior Software Engineer and Tech Lead at Google, who, according to her own site, is “working on new features for Gmail and Gmail Ads?” (Google is currently facing some heat over how it exploits Gmail user data for advertisers – but they would never exploit user data to help the Obama campaign, right?)

Probst and Ghani not only went to undergrad at the University of the South and grad school at Carnegie Mellon University together, but they have also co-authored two refereed journal articles together and presented four conference papers together. Something tells me their paths have crossed a time or two, including while Ghani was on the campaign.

Many Google employees personally volunteered for Ghani’s team – the question for conservatives is what exactly did they do? I bet Ethan Roeder, OFA Director of Data could tell us. Before joining the Obama campaign, Roeder was the Director of Data, Technology, and Election Administration at the Voting Information Project (PDF), a “Collaboration between Google, Pew Center on the States,” and the New Organizing Institute, according to Roeder’s LinkedIn profile.

Speaking of people at Google volunteering time and resources, I can’t imagine Catherine Bracy, OFA Community Outreach Lead, Product Manager, Tech4Obama Program Manager, and co-director of Obama’s San Francisco technology field office doesn’t have a direct line to some of the key decision makers at Google who would approve employee sabbaticals to work on campaigns. Bracy, according to her LinkedIn profile, was an administrative director at Harvard’s Berkman Center for Internet & Society, which receives millions in funding from Google.

Why does that matter?

Well, Bracy’s primary responsibilities at Berkman Center “included oversight of the center’s budgets and operations, fundraising, project management and event planning.” Ostensibly, she was involved in asking Google for the money it paid to support Berkman – what a great asset for a presidential campaign to have, huh? It was such a great asset, in fact, that Obama received over $719,000 in donations from Google employees, helping him on the path to an average 6:1 fundraising advantage over Romney from the Silicon Valley area.

And that kind of money advantage is, in fact, the direct result of Bracy’s work for the campaign, if Mother Jones has anything to say about it:

Bracy reached out to heavyweights in the Bay Area’s digital world, from Craiglist to Google, before helping to launch the Obama campaign’s San Francisco technology field office last March.

And The Atlantic reported last year that Bracy and others were considered to be the “stars” of several closed-door fundraisers targeting the technology community:

In late January, Goff, Reed, and Bracy hosted a fundraiser at San Francisco’s Founders Den, a SoMa working space and private club. Thirty dollars got donors into a panel reception, and $500 gave them access to a “small roundtable discussion” starting an hour and a half earlier.

The Atlantic report also notes “The Obama campaign wasn’t interested in commenting on this sort of thing.” THERE’s a big shocker….

Bracy also brags on her LinkedIn profile that she personally was responsible for recruiting over 100 volunteers from the Silicon Valley community for the campaign, and oversaw the development of 14 products. That list of volunteers may (or may not have) included:

All I’m saying is that, maybe when people from Google, or from Salon.com, which just happen to be owned by Robert McKay, Chairman of the left wing donor activist group, Democracy Alliance (along with, unsurprisingly, another former Google employee), deny that Google collaborates with Democrats, maybe we shouldn’t just take their word for it.